"but sometimes the software isn't up to date."

if you ever get software from outside sources
you would need to check the license of the software to ensure its libre

also its a good idea to compile the program yourself
as this is much more secure and will ensure you have the absolute latest version

"This makes me wonder, if there is a way for Trisquel to do a sweep to check if my installed software is Libre?"
currently only for the deb packages
there is a program call vrms(virtual Richard stallman)
that lists any deb packages installed that are non-free by the Debian free software guidelines

but this program is controversially and quite incorrectly named as it goes on Debians free software guidelines not the fsf's and is inconsistent with RMS's

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